Through bravado and persistence, Mr. Robert asserted his place in Washington's business firmament from an unlikely starting place. He had barely muddled through high school and was kicked out of college for fighting, rendering him homeless for more than a month. He worked as a bouncer, sold encyclopedias and unloaded freight trucks — then had an epiphany.

Convinced that he was throwing away his life, Mr. Robert decided to go into the real estate business and focus on distressed assets. He bought handfuls of real estate books and started purchasing condos in Beltsville when he was 20. In 1981, he went to nearly 20 Washington-area banks, seeking a $500,000 loan to start an asset management company — despite advice that the recession at the time made such a business venture unwise.

Riggs National Bank finally agreed to pony up the money after Mr. Robert told the loan officer, “I'm going to be the biggest real estate workout guy in town.”

He was right. In one of his most publicized deals, his J.E. Robert Cos. in 1990 won a government contract worth $41 million over three years to sell a grab bag of strip malls, apartment complexes and other assets worth billions of dollars and held by failed savings-and-loans in Texas. The deal was part an unprecedented effort by the Resolution Trust Corp., which oversaw the enormous S&L bailout, to recruit private asset management companies.

Mr. Robert really hit it big in the 1990s, with assets and offices stretching around the globe. At one point, he estimated his wealth at about $1 billion. Mr. Robert was running deals in so many time zones that he had a special ski helmet built with a cellphone in it so he could work while racing down the slopes.

Mr. Robert lived large. He had homes from Potomac to Colorado and a list of friends that ranged from Oprah Winfrey to the rock star Bono, from Middle East sheiks to Russian oligarchs. He squired glamorous women across the Mediterranean, survived a helicopter explosion in Antarctica and explored the Colombian jungle in search of guerrilla fighters.

His friend James Kimsey, summed it up this way: “Somehow he intuitively thought, ‘Life is too short to drink bad wine.' ”

His most prized possession: a piece of string from the garment of a Colombian tribal chief. He wore it tied around his wrist and was told it would connect him to his spirit. Receiving the string “was one of the most remarkable experiences of my life,” Mr. Robert told Washington Business Journal. “I gave him the Gucci sunglasses I was wearing.”